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O-TBDPS-D-Thr-N-Boc-L-tert-Leu-Diphenylphosphine
(CAS RN:1264520-63-9 Product Number:T2937)

Structure

O-TBDPS-D-Thr-N-Boc-L-tert-Leu-Diphenylphosphine
Synonym N-Boc-L-tert-leucine N-[(2R,3S)-3-(tert-Butyldiphenylsilyloxy)-1-(diphenylphosphino)-2-butyl]amide
Synonym N-(tert-Butoxycarbonyl)-L-tert-leucine N-[(2R,3S)-3-(tert-Butyldiphenylsilyloxy)-1-(diphenylphosphino)-2-butyl]amide

General Information

Product Number T2937

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Purity/Analysis Method >98.0%(HPLC)
Storage Temperature
M.F. / M.W. C43H57N2O4PSi=725.00
CAS RN 1264520-63-9
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Specification

Purity(HPLC) min. 98.0 area%
Elemental analysis(Nitrogen) 3.60 to 4.00 %
Specific rotation [a]20/D -26.0 to -29.0 deg(C=1、CHCl3)

References

Reaxys-RN 21221495
PubChem SID 172089008

Transport Information

HS Number 2931399090

Application

A Novel Dipeptide-Based Chiral Phosphine Organocatalyst for Asymmetric Cyclization

Typical procedure (entry 1: R = CH3CH2CH2-): To a dried round bottom flask is added N-butylidene-P,P-diphenylphosphinic amide (27.1 mg, 0.1 mmol), O-TBDPS-D-Thr-N-Boc-L-tert-Leu-diphenylphosphine (3.6 mg, 0.005 mmol) and MS5Å (60 mg) under N2, followed by the addition of anhydrous Et2O (1 mL). The reaction mixture is cooled to 0 ºC, tert-butyl 2,3-butadienoate (22 micro-L, 0.15 mmol) is then added, and the mixture is stirred at 0 ºC for 30 min. The reaction mixture is then filtered (to remove MS5Å) and concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: hexane/EtOAc = 10:1 to 2:1) to afford the cycloaddition product (37.9 mg, 92% yield, 96% ee) as a colorless oil.

References

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